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Amide‐to‐Ester Substitution Allows Fine‐Tuning of the Cyclopeptide Conformational Ensemble
Author(s) -
Cupido Tommaso,
Spengler Jan,
RuizRodriguez Javier,
Adan Jaume,
Mitjans Francesc,
Piulats Jaume,
Albericio Fernando
Publication year - 2010
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200907274
Subject(s) - substitution (logic) , amide , chemistry , stereochemistry , combinatorial chemistry , computational biology , computer science , biochemistry , biology , programming language
Without affecting the overall 3D structure , amide‐to‐ester backbone substitution (or ester scan) exerts a pronounced influence on the conformational equilibrium of the RGD cyclopeptide cilengitide and its derivatives (see figure; RGD=Arg‐Gly‐Asp). The appropriate substitution, which stabilized the receptor‐complementary conformations, improved the biological activity of this integrin antagonist.